N,N{40 -bridged-bis{8 2-alkyl-2-hydroxyethylamine{9 salts

ABSTRACT

N,N&#39;&#39;-Bridged-Bis(2-alkyl-2-Hydroxyethylamine)salts of the formula   are prepared by condensing an epoxide of the formula   and a diamine of the formula R&#39;&#39;NH-X-NHR&#39;&#39;. The products and dicarbanilates, acid-addition salts, N,N&#39;&#39;-dioxides and N,N&#39;&#39;diammonium quaternary salts derived therefrom have antibacterial activity in vitro and are useful as antibacterial agents.

United States Patent [191 Diana et a1.

[ 1 Dec. 23, 1975 N,N-BRIDGED-BIS[2-ALKYL-2- HYDROXYETHYLAMINE1SALTS [75] Inventors: Guy D. Diana, Stephentown; Royal A. Cutler, Sand Lake, both of NY.

[63] Continuation-impart of Ser. No. 123,097, March 10,

1971, abandoned.

[52] US. Cl 260/50L17; 260/501.2; 260/584 R;

424/325 [51] Int. Cl. C07C 91/02 [58] Field of Search 260/501.2, 584 R, 501.17

[56] References Cited UNITED STATES PATENTS 3,131,220 4/1964 Zirkle 260/583 3,524,883 8/1970 Kersnar et al 260/584 R FOREIGN PATENTS OR APPLICATIONS 1,220,438 7/1966 Germany 1,411,269 8/1965 France Primary Examiner-James 0. Thomas, Jr. Assistant Examiner-G. Breitenstein Attorney, Agent, or FirmTheo'dore C. Miller; B. Woodrow Wyatt [57] ABSTRACT N,N'-Bridged-Bis[2-alkyl-2-I-Iydroxyethylamine]salts of the formula are prepared by condensing an epoxide of the formula and a diamine of the formula R'NI-IXNHR. The

products and dicarbanilates, acid-addition salts, N,N'- dioxides and N,N-diammonium quaternary salts derived therefrom have antibacterial activity in vitro and are useful as antibacterial agents.

14 Claims, No Drawings N,N'-BRIDGED-BIS[2-ALKYL-2-HYDROXYE- THYLAMINE ]SALTS This application is a continuation-in-part of our copending application Ser. No. 123,097, filed Mar. 10, 1971, and now abandoned,

This invention relates to compositions of matter classified in the art of organic chemistry as N,N-bridgedbis-[(0 and/or N-substituted)-2-alkyl-2-hydroxyethylamines] and to a process for preparing them.

In its composition of matter aspect our invention provides N,N-(X)-bis[N-(R)-2-(R)-2-(ZO)-ethylamine] of the formula ZO R R OZ wherein:

R is alkyl of three to carbon atoms or cycloalkyl of four to seven ring carbon atoms;

R is hydrogen or atertiary alkyl of one to four carbon atoms;

X is alkylene of two to 12 carbon atoms with bonds to the nitrogen atoms at different carbon atoms or X-Y-X, wherein X and X" are alkylene of one to four carbon atoms with bonds to Y and to the nitrogen atoms at the same or different carbon atoms and Y is cycloalkylene of four to seven ring carbon atoms with bonds to X and x at the same or different carbon atoms, phenylene, vinylene or ethynylene;

the sum of the number of carbon atoms of R and X is at least nine;

Z is hydrogen or, when R is atertiary alkyl of one to four carbon atoms, N-phenylcarbamoyl or N- phenylcarbamoyl substituted in the benzene ring by one to three members selected from the group consisting of atertiary alkyl of one to four carbon atoms, halo and atertiary alkoxy of one to four carbon atoms or by a member selected from the group consisting of trifluoromethyl, acetamido, nitro, and methylsulphonyl;

acid-addition salts thereof; and,

when R is atertiary alkyl of one to four carbon atoms and Z is hydrogen, N,N'-dioxides, N,N-di(atertiary alkyl of one to four carbon atoms)diammonium quaternary salts and N,N-dibenzyldiammonium quaternary salts thereof.

The compounds of Formula I and acid-addition salts, N,N'-dioxides and N,N'-diammonium quaternary salts thereof have antibacterial activity in vitro and are useful as antibacterial agents.

In its process aspect our invention provides the process for preparing N,N'-(X)-bis[N-(R')-2-(R)-2-(ZO)- ethylamine] of Formula I, wherein Z is hydrogen, which comprises condensing an epoxide of the formula with a diamine of the formula R'NH-X-NHR' (Formula llI), wherein R of Formula II and R and X of Formula III have the same meanings ascribed thereto in Formula 1.

(Formula II) When R is alkyl of three to fifteen carbon atoms, it is normal alkyl or branched alkyl as illustrated by propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl and pentadecyl. Since R and ethyl are integral, they are named integrally when R is alkyl. Thus, the illustrated alkyls become respectively, pentyl, 3-methylbutyl, hexyl, 4-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl and heptadecyl.

When R is cycloalkyl of four to seven ring carbon atoms, it is cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.

When R is atertiary alkyl of one to four carbon atoms, it is methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.

When X is alkylene of two to twelve carbon atoms with bonds to the nitrogen atoms at different carbon atoms, it can be unbranched or branched'. If unbranched, X is l,2-ethylene, 1,3-propylene, l,4-butylene, l,5-pentylene, 1,6-hexylene, 1,7-heptylene, 1,8- octylene, 1,9-nonylene, l,lO-decylene, 1,1 l-undecylene or l,I2-dodecylene. If branched, X is, for example, l,2-propylene, 2,4-butylene, 2,10-dodecylene, or 2-methyl-l ,4-butylene.

When X is X'--Y-X, X and X" can be the same or different and can be unbranched or branched alkylene of one to four carbon atoms with bonds to Y and to the nitrogen atoms at the same or different carbon atoms as illustrated by methylene, ethylene, ethylidene or l,4-butylene. When Y is cycloalkylene of four to seven ring carbon atoms with bonds to X and X" at the same or different carbon atoms, it is, for example, cyclobutylidene, l,4-cyclohexylene or l,2-cycloheptylene. When Y is cycloalkylene or vinylene, the bonds to X and X can be cis or trans. Thus, X'-Y-X" is, for example, l,3-cyclobutylenebismethyl, l,4-cyclohexylenebismethyl, cis-l,4-cyclohexylenebismethyl, transl,4-cyclohexylenebismethyl, l,2-cycloheptylenebismethyl, cyclohexylene-l-methyl-4-(2-ethyl), -cyclohexylenel -methyl-4-( l-ethyl), cyclohexylene-l methyl-4-(4-butyl), l,4-phenylenebismethyl, trans-l ,4- (2-butenylene) and l,4-(2-butynylene).

When Z is N-phenylcarbamoyl substituted in the benzene ring, it is, for example, N-(o-tolyl)carbamoyl, N-(p-bromophenyl)-carbamoyl, N-(m-methoxyphenyl)carbamoyl, N-(4-chloro-o-tolyl)carbamoyl, N-(5-chloro-2,4-dimethoxyphenyl)carbamoyl, N-[m- (trifluoromethyl)phenyl]carbamoyl, N-(p-acetamidophenyl)carbamoyl, N-(m-nitrophenyl)carbamoyl, or N-[p-(methylsulfonyl)phenyllcarbamoyl. Named as substituted carbanilates the illustrated substituted N- phenylcarbamoyls are, respectively, o-methylcarbanilate, p-bromocarbanilate, m-methoxycarbanilate, 2- methyl-4-chlorocarbanilate, 5-chloro-2,4-dimethoxycarbanilate, m-(trifluoromethyl)carbanilate, pacetamidocarbanilate, m-nitrocarbanilate and p-(methylsulfonyl)carbanilate. When N-phenylcarbamoyl is substituted in the benzene ring by halo, halo is fluro, chloro, bromo or iodo.

In N,N-diammonium quaternary salts of the compounds of Formula I wherein R is alkyl, atertiary alkyl of one to four carbon atoms can be methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.

The manner and process of making and using the invention and the best mode of carrying it out will now be described so as to enable any person skilled in the 3 art to which it pertains to make and use it.

The preferred method for carrying out the process of condensing an epoxide of Formula ll with a diamine of Formula III is the use of a solvent inert under the reaction conditions, for example, acetonitrile, benzene, chloroform, N,Ndimethylformamide, ethanol, methanol or tetrahydrofuran at a temperature in the range of to 100C. Methanol is the preferred solvent and room temperature is the preferred temperature.

Compounds of Formula I in which R is methyl are also prepared by methylating the corresponding compounds of Formula I in which R is hydrogen with formaldehyde and formic acid.

Phenylcarbamoylation and phenylthiocarbamoylation of compounds of Formula I wherein R is alkyl and Z is hydrogen, formation of acid-addition salts of the compounds of Formula I, and N,N' dioxidation and N-N'-diquaternerization of the compounds of Formula I wherein R is alkyl are all accomplished by standard methods.

The phenylisocyanates and phenylisothiocyanates required for phenylcarbamoylation and phenylthiocarbamoylation are known classes of compounds, some of which are commercially available. Those (substitutedphenyl)isocyanates which are not commercially available can be prepared, for example, by passing carbonyl chloride into hot solutions of the corresponding anilines in toluene, saturated with hydrogen chloride. Those (substituted-phenyl)isothiocyanates which are not commercially available can be prepared, for example, by treating the corresponding ammonium (substituted-phenyl)dithiocarbamates, prepared in turn from the corresponding substituted anilines, carbon disulfide and ammonia, with lead nitrate.

Acid-addition salts of the compounds of Formula I can be prepared with any pharmaceutically acceptable inorganic (mineral) or organic acid. lf inorganic, the acid can be, for example, hydrochloric acid, hydrobromic acid, nitric acid, phosphoric acid or sulfamic acid. lf organic, the acid can be, for example, acetic acid, glycolic acid, lactic acid, quinic acid, hydrocinnamic acid, succinic acid, tartaric acid, citric acid, methanesulfonic acid or benzenesulfonic acid.

N,N'-diammonium quaternary salts of compounds of Formula I wherein R is alkyl can be prepared with any pharmaceutically acceptable atertiary one-to-four-carbon alkyl or benzyl ester of a strong inorganic or organic acid, for example, methyl chloride, methyl io dide, ethyl p-toluenesulfonate, propyl bromide, isobutyl iodide or benzyl bromide.

That the acid and the alkyl ester be pharmaceutically acceptable means that the beneficial properties inherent in the free base not be vitiated by side effects ascribable to the anions.

Although pharmaceutically acceptable salts are preferred, all salts are within the scope of the invention. A pharmaceutically unacceptable salt may be useful, for example, for purposes of identification or purification or in preparing a pharmaceutically acceptable salt by ion-exchange procedures.

The intermediate epoxides of Formula ll are a known class of compounds. Their preparation is accomplished by epoxidation of the corresponding l-alkenes and vinylcycloalkanes by any of several well-known methods, for example, by the use of peracetic acid buffered with sodium acetate. The l-alkenes and vinylcycloalkanes are known compounds, some of which are commercially available.

The intermediate diamines of Formula II] are also a known class of compounds, some of which are commercially available. Preparation of those which are not commercially available is accomplished by well-known methods, for example, by reductive amination of the corresponding diketone or dialdehyde, amination of the corresponding dihalide or dialcohol p-toluenesulfonate diester or reduction of the corresponding dinitrile, dioxime, diamide, diazide or other di-higher-oxidation-state nitrogen compound. Unsymmetrical diamines can be prepared from unsymmetrical starting materials.

The compounds of Formula I and acidaddition salts, N,N-dioxides and N,N'-diammonium quaternary salts thereof are purified by distillation or by recrystallization. Their structure follow from their route of synthesis and are corroborated by infrared spectral analysis and by the correspondence of calculated and found values of elemental analysis of representative samples.

As stated above the compounds of Formula I and acid-addition salts, N,N-dioxides and N,N-diammonium quaternary salts thereof have antibacterial activity in vitro, which was determined by a standard serial dilution test. In this test the concentration of compound arresting the growth of the microorganism is the bacteriostatic concentration and is expressed in parts per million (p.p.m.). The concentration of compound preventing growth of the microorganism after further incubation is the bactericidal concentration and is also expressed in parts per million.

The compounds of Formula I and acid-addition salts, N,N"dioxides and N,N'-diammonium quaternary salts thereof are useful as antibacterial agents and are espe cially useful for disinfecting and sanitizing living and non-living surfaces by conventional swabbing, padding, spraying, immersing, rinsing and the like techniques. Depending on the particular purpose involved, the compounds are used in aqueous solution, in aqueous detergent solutions or in solutions in organic solvents.

The following examples illustrate specific embodiments of our invention without limiting the latter thereto.

EXAMPLE 1 A solution of l-undecene oxide (88.8 g.), hexamethylenediamine (l,6-hexanediamine, 30.3 g.) and methanol (400 ml.) was allowed to stand at 0C. overnight, then at room temperature over the weekend. The solid was collected and recrystallized from ethanol, affording N,N'-( l ,6-hexylene )-bis[2-hydroxyundecylaminel (l: R CH (CH R H, X (CH Z l-l)(m.p. 122.6-l29.0C.).

Hydrogen bromide was bubbled through a solution of N ,N-( l ,6-hexylene )-bis[2-hydroxyundecylamine] (5 g.) in methanol ml.). The resulting solid was collected (4.6 g.) and recrystallized from methanol, affording N,N'-( l ,6-hexylene)-bis[2-hydroxyundecylamine] dihydrobromide (2.4 g., m.p. 29930lC.).

A solution of N,N'-(l,6-hexylene-bis[2-hydroxyundecylamine] (5 g.), glycolic acid (1.66 g.) and methanol was heated until the solids dissolved, then evaporated to dryness. Recrystallization of the solid from acetone afforded N,N-(l,6-hexylene)-bis[2-hydroxyundecylamine] diglycolate (4.6 g., m.p. 88.294.6C.).

[n a similar manner using acetic acid and lactic acid instead of glycolic acid there were obtained, respectively, N ,N l ,6-hexylene )-bis[2-hydroxyundecylamine] diacetate (m.p. ll3-l20.6C.) and N,N-(l,6- hexylene)-bis[2-hydroxyundecylamine] dilactate (m.p. l02.0-l04.0C.).

Using hydrochloric acid, nitric acid, phosphoric acid,

sulfamic acid, quinic acid, hydrocinnamic acid, succinic acid, tartaric acid, citric acid, methanesulfonic acid and benzenesulfonic acid, there are obtained, respectively:

N,N'-( l ,6-hexylene)-bis[Z-hydroxyundecylamine] dihydrochloride; N,N l ,6 hexylene )-bis[2-hydroxyundecylamine] dinitrate; N,N'-( l ,6-hexylene)-bis[Z-hydroxyundecylamine] diphosphate; N,N l ,6-hexylene)-bis[2-hydroxyundecylamine] disulfamate; N,N'-( l,6-hexylene)-bis[2-hydroxyundecylamine1 I diquinate;

N,N-( l ,6-hexylene)-bis[ 2-hydroxyundecylamine] dihydrocinnamate; I N,N'-( l ,6-hexylene )-bis[2-hydroxyundecylamine] succinate; .N,N' l ,6-hexylene)-bis[Z-hydroxyundecylamin] tartrate; v N,N-( l ,6-hexylene)-bis[2-l1ydroxyundecylamin e] dicitrate; 'N,N'-( l ,-hexylene )-bis[Z-hydfoxyundecylarhine] dimethanesulfonate; and N,N'-( l ,6-hexylene )-bis[2hydroxyundecylamine] dibenzen'esulfonate. I I I Table I shows the results of the antibacterial testing in vitro of N,N-(l,6-hexylene)-bis[2-hydroxyundecylamine]. A

Condensation of l-pentene oxide and hexamethylenediamine affords,N,N'-( l,6-hexylene)-bis[2-hydrox- EXAMPLE 3 Condensation of 3-methyl-l-butene oxide and hexamethylenediamine affords N,N-(l,6-hexylene)-bis[2- hydroxy-3-methylbutylamine] (I: R (CH CH, R

, EXAMPLE 4 Condensation of l-hexene oxide and hexamethylene- 'diamine affords I N,N-( l ,6-hexylene)-bis[2-hydroxyhexylamine] (I: R CH (CH R.= H, X (CH 'Z'=H). v

EXAMPLES Condensation of 4-methyl-l-pentene oxide and hexamethylenediamine affords N,N-(l,6-hexylene)-bis[2- hydroxy-4-methylpentylamine] (I: R (CH CHCH R H, X (CH Z H).

EXAMPLE 6 Condensation of 3-methyl-1-pentene oxide and hexamethylenediamine affords N,N-(l,6-hexylene)-bis[2- hydroxy-3-methylpentylamine] (I: R CH CH (CH )C, R H, X (CH Z H).

EXAMPLE 7 EXAMPLE 8 In a manner similar to that of Example 1, condensation of l-heptene oxide (71.8 g.) and hexamethylenediamine (32 g.) and recrystallization of the resulting product from ethanol gave N,N'-( l,6-hexylene)-bis[2- (CH2)6, z H) (16.5 g., m.p.' 131.2 134.2c.

EXAMPLE 9 In a manner similar tothat of Example 1, condensation of l-octene oxide (42 g.) and hexamethylenediamine (19.05 g.) and recrystallization of the resulting product from methanol gave N,N-( l,6-hexylene)- bis[2-hydroxyoctylamine] (I: R CH (CH R H, X (CH Z H) (17.2 g., m.p. l24.0-l27.4C.).

EXAMPLE 10 In a manner similar to thatof Example 1, condensation of lnonene oxide (97.4 g.) and hexamethylenediamine (39.8 g.) and recrystallization of theresulting product (67 g.)'frorn ethanol-afforded N,N'-(l,6-hexylene)-bis[2-hydroxynonylamine] (l: R CH (CH R H, X l22l29.2C.).

Treatment of N,N-(l,6-hexylene)-bis[2-hydroxynonylamine] (4g) with lactic acid"(2.l2 g.)'in methanol and recrystallization of the resulting salt from ac'etone gave N,N-(l,6-hexylene)-bis[2-hydroxynoriylamine] dilactate (3.3 g., m.p. lO3.0 l04.6C.).

EXAMPLE 11 'In a manner similar to that of Example 1, condensation of l-decene oxide (50 g.) and hexamethylenediamine (l8.6 g.) and recrystallization of the resulting product from methanol gave N,N-(l,6-hexylene)- bis[2-hydroxydecylarnine] (I: R CH (CH R H, X (CH Z H) (25.4 g., m.p. ll8.0-l26.8C.).

EXAMPLE 12 In a manner similar to that of Example 1, condensation of l-dodecene oxide (50 g.) and hexamethylenediamine (15.8 g.) and recrystallization of the resulting product from ethanol gave N,N'-(l ,6-hexylene)-bis[2- 2)fi, Z H) (35 g., m.p. 123.6-l28.0C.).

EXAMPLE l3 Condensation of ltridecene oxide and hexamethylenediamine affords N,N'-( l ,6-hexylene)-bis[2-hydroxytridecylamine] (l: R CH (CH R H, X zls Z EXAMPLE 14 In a manner similar to that of Example 1, condensation of l-tetradecene oxide (91.8 g.) and hexamethyl- (CH H) (67 g., m.p.

enediamine (25 g.) and recrystallization of the resulting product (71 g., m.p. ll8l2lC.) from ethanol gave N,N-( 1 ,6-hexylene)-bis[2-hydroxytetradecylamine] (I: R CH (CH R H, x (CH Z =H) (55.3 g., m.p. 122126C.).

EXAMPLE l5 EXAMPLE 16 Condensation of l-hexadecene oxide and hexamethylenediamine affords N,N-( l ,6-hexylene)-bis[2- hydroxyhexadecylamine] (I: R CH (CH R H, X (CH2)6, Z H).

EXAMPLE 17 Condensation of l-heptadecene oxide and hexamethylenediamine affords N,N-( l ,6-hexylene)-bis[2- hydroxyheptadecylamine] (I: R CH (CH R H, X (CH Z H).

EXAMPLE l8 Condensation of vinylcyclobutane oxide and hexamethylenediamine affords N,N-(I,6-hexylene)-bis[2- hydroxy-2-cyclobutylethylamine] (I: R CH (CH CH, R H, X (CH Z H). J

EXAMPLE l9 Condensationof vinylcyclopentane oxide and hexamethylenediamine affords N,N-(l,6-hexyIene)-bis[2- hydroxy-2-cyclopentylethylamine] (I: R CH (CH CH, R H, X (CH Z H).

EXAMPLE Condensation of vinylcyc'lohexane oxide and hexamethylenediamine affords N,N'-( l ,6-hexylene)-bis[2- hydroxy-2-cyc]ohexylethylamine] (I: R CH (CH CH, R H, X (CH Z H).

EXAMPLE 21 Condensation of vinylcycloheptane oxide and hexamethylenediamine affords N,N'-( l,6-hexylene)-bis[2- hydroxy-2-cycloheptylethylamine] (I: R CH (CH CH, R' H, X (CI-1 Z H).

EXAMPLE 22 A. N,N-( l ,6-Hexylene)-bis[2-hydroxyundecylamine] (25.6 g.) was added in portions to a solution of formic acid (98%, 25 ml.) and formaldehyde (60%, 15 ml.) held at 70C. When the addition was complete the resulting solution was refluxed (9 hr.), then basified with sodium hydroxide solution (35%). The solid was collected and treated with methanolic potassium hydroxide. The mixture was diluted with water and extracted with ether. Concentration of the ether extract and distillation of the residue under vacuum afforded an oil (16 g., b.p. 208-2l4C./0.05 mm.). Hydrogen bromide was bubbled through an ethereal solution of the oil. The resulting solid was recrystallized from etherisopropyl alcohol, affording N,N-( l ,6-hexylene)- bis[N-methyl-Z-hydroxyundecylamine] dihydrobro- 8 mide (I: R=CH (CI-I R CH X= (CH Z= H) (m.p. I86.4I89.8C.).

B. Condensation of l-undecene oxide and N,N- dimethylhexamethylenediamine and treatment of the resulting product with hydrogen bromide also affords N,N-( l ,6-hexylene )-bis-[N-methyl-Z-hydroxyundecylamine] dihydrobromide.

Table II shows the results of the in vitro anti-bacterial testing of N,N-( l,6-hexylene)-bis[N-methyl-2-hydroxyundecylamine] dihydrobromide.

Table II Bacteriostatic Bactericidal Microorganism concentration concentration (p.p.m.) (p.p.m.)

Staphylococcus aureus 2.5 7.5 Eberthella typhi 5 5 Clostridium welchii 5 5 Pseudomonas aeruginasa 25 5O EXAMPLE 23 Condensation of l-undecene oxide and N,N-diethylhexamethylenediamine affords N,N'-(l,6-hexylene) bis[N-ethyI-2-hydroxyundecylamino] (I: R CH (CH R CH CH X (CH Z H).

EXAMPLE 24 Condensation of l-undecene oxide and N,N- dipropylhexamethylenediamine affords N,N-( l ,6-hexylene)-bis[N-propyl-2-hydroxyundecylamine] (I: R 3( z)a 3( 2)z X M Z EXAMPLE 25 Condensation of l-undecene oxide and N,N-di(isopropyl)hexamethylenediamine affords N,N-(l,6-hexylene)-bis-[N-isopropyl-2-hydroxyundecylamine] (I: R CH (CH R (CI-I CH, X (CH Z H).

EXAMPLE 26 Condensation of l-undecene oxide and N,N-dibutylhexamethylenediamine affords N,N'-(l,6-hexylene)- bis[N-butyl-2-hydroxyundecylamine] (I: R 3( z)s 3( z)3, X -M6 Z EXAMPLE 27 Condensation of l-undecene oxide and N,N- di(isobutyl)hexamethylenediamine affords N,N'-( l ,6- hexylene)-bis[N-isobutyl-2-hydroxyundecylamine] (I: R CH (CH R (CH CHCH X (CH Z H).

EXAMPLE 28 Condensation of l-undecene oxide and N,N-di(secbutyl)hexamethylenediamine affords N,N-(l,6-hexylene)-bis-[N-(sec-butyl)-2-hydroxyundecylamirle] (I: R CH (CH R CH CH (CI-I )CH, X (CH Z H).

EXAMPLE 29 EXAMPLE so In a manner similar to that of Example 22, methylation of N,N'-(l,6-hexylene)-bis[2-hydroxyoctylamine] (35 g.) and treatment of the resulting product (b.p. 177-l 82C./l mm.) with hydrogen bromide gave N,N'-( I ,6-hexylene)-bis[N-methy1-2-hydroxyocty1amine] (I: R CH (CH R CH X (CH Z H) dihydrobromide (19.1 g., m.p. l67.0168.8C.).

EXAMPLE 31 In a manner similar to that of Example 22, methylation of N,N'-( l ,6-hexylene )-bis[ 2-hydroxynonylamine] (36 g.) and treatment of the resulting product (25 g., b.p. l72l76C./0.05 mm.) with hydrogen bromide gave N,N-(l,6-hexylene)-bis-[N-methyl-2- hydroxynonylamine] (I: R CH (CH R CH X (CH Z H) dihydrobromide (26.3 g., m.p. l76.0--l77.0C.).

EXAMPLE 32 In a manner similar to that of Example 22, methylation of N,N-(1,6-hexylene)-bis[2-hydroxydecylamine] (36.7 g.), treatment of the resulting product (17.5 g., b.p. 204206C./0.03 mm.) with hydrogen bromide and recrystallization of the resulting salt from isopropyl alcohol gave N,N-(l,6-hexylene)-bis[N- methyl-2-hydroxydecy1amine] (I: R CH (CH R CH X (CH Z H) dihydrobromide (8.4 g., m.p. l86.0-l87.6C.).

EXAMPLE 33 EXAMPLE 34 lna manner similar to that of Example 22, methylation of N,N'-( l ,6-hexylene )-bis[2-hydroxytetradecylamine] (30 g.) gave N,N'-(l,6-hexylene)- bis[N-methyl-2-hydroxytetradecylamine1 (I: R CH (CH R CH X (CH Z H) as a brown oil (28.2 g.).

EXAMPLE 35 In a manner similar to that of Example 1, condensation of l-decene oxide (100 g.) and ethylenediamine (19.2 g.) and recrystallization of a portion (20 g.) of the resulting solid (45' g.) from ethanol gave N,N- ethylenebis[Z-hydroXydecylamine] (I: R CH (CH R H, X (CH Z H) (13.6 g., m.p. l40.0-145.8C.).

EXAMPLE 36 In a manner similar to that of Example 1, condensation of l-undecene oxide (40 g.) and ethylenediamine (7.07 g.) and two recrystallizations of the resulting solid (14.9 g.) from ethanol gave N,N-ethylenebis [2-hydroxyundecylaminel] (I: R CH (CH R H, X =(CH 2: H) (12.4 g., m.p. l30.2-l37.8C.).

EXAMPLE 37 In a manner similar to that of Example 1, condensation of l-dodecene oxide (100 g.) and ethylenediamine (16.3 g.) and recrystallization of part (20 g.) of the resulting product (55.3 g.) from methanol gave N,N- ethylenebis[2-hydroxydodecylamine] (I: R CH (CH R H, X (CH Z== H) (13.4 g., m.p. 137.0-l42.0C.).

EXAMPLE 38 In a manner similar to that of Example 22, methylation of N,N'-ethylenebis[Z-hydroxydecylamine] (15 g.) and treatment of the resulting product with hydrogen bromide gave N,N'-ethylenebis[N-methyl-2- hydroxydecylamine] (I: R CH (CH R CH X (CH Z H) dihydrobromide (4.0 g., m.p. l52.0l64.0C.).

EXAMPLE 39 In a manner similar to that of Example 22, methylation of N,N-ethylenebis[2-hydroxyundecylamine] (30 g.), treatment of the resulting product with hydrogen bromide and recrystallization of the resulting salt from isopropyl alcohol gave N,N-ethylenebis[N-methyl-2-hydroxyundecylamine](I: R CH (CH' R CH X (CH Z H) dihydrobromide (12.8 g., m.p. 151.0l62.0C.).

EXAMPLE 40 In a manner similar to that of Example 22, methylation of N,N-ethylenebis[2-hydroxydodecylamine] (35 g.), treatment of the resulting product with hydrogen bromide and recrystallization of the resulting salt from isopropyl alcohol gave N,N'-ethylenebis[N-methyl-2-hydroxydodecylamine] (I: R CH (CH R CH X (CH Z H) dihydrobromide (4.6 g., m.p. 162.0C.).

EXAMPLE 41 In a manner similar to that of Example 1, condensation of l-nonene oxide (120 g.) and 1,3-propanediamine (31.2 g.) and two recrystallizations of the resulting product from methanol gave N,N-( l ,3-propylene)- bis[Z-hydroxynonylamine] (I: R CH (CH R H, x (CH z H) 13.2 g., m.p. 107.0-109.0c.

EXAMPLE 42 In a manner similar to that of Example 1, condensation of l-decene oxide (58 g.) and 1,3-propanediamine (13.8 g.) and three recrystallizations of the resulting product from methanol gave N,N-(l,3-propylene)- bis[2-hydroxydecylamine] (l: R CH (CH R H, X (CH Z H) (8.5 g., m.p. 104.0- 107.6C.).

EXAMPLE 43 In a manner similar to that of Example 1, condensation of l-undecene oxide (104.6 g.) and 1,3- propanediamine (22.7 g.) and two recrystallizations of the resulting product from methanol gave N,N-(l,3- propylene)-bis[2-hydroxyundecylamine] (l: R cH cH R H, X (CH z H) 29.0 g., m.p. 94.0103.0C.).

EXAMPLE 44 In a manner similar to that of Example 1, condensation of l-dodecene oxide g.) and 1,3-propanediamine (20.1 g.) and three recrystallizations of the result- 11 ing product from isopropyl alcohol gave N,N-(l,3- propylene)-bis[2-hydroxydodecylamine] (I: R CH (CH R H, X (CH Z H) (11.9 g., 96.0l06.0C.).

EXAMPLE 45 In a manner similar to that of Example 22, methylation of N,N'-(l,3-propylene)-bis[2-hydroxynonylamine] (14 g.), treatment of the resulting product with hydrogen bromide and two recrystallizations of the resulting salt from acetonitrile gave N,N-(1,3- propylene)-bis[N-methyl-2-hydroxynonylamine] (I: R CH (CH R CH X (CH Z H) dihydrobromide (9.1g, m.p. l75.0189.OC.).

EXAMPLE 46 In a manner similar to that of Example 22, methylation of N,N'-(1,3-propylene)-bis[2-hydroxydecylamine] (21.4 g.), treatment ofthe resulting product with hydrogen bromide and four recrystallizations of the resulting salt from ethyl acetate-isopropyl alcohol gave N,N'-( 1 ,3-propylene)-bis[N-methyl-2-hydroxydecylamine] (I: R CH (CH R CH X (CH Z H) dihydrobromide (9.0 g., m.p. '174.2184.0C.).

EXAMPLE 47 In a manner similar to that of Example 22, methylation of N,N'-( l ,3 -propylene)-bis[2-hydroxyundecylamine] (16 g.), treatment of the resulting product with hydrogen bromide and recrystallization of the resulting salt from acetone gave N,N-(1,3-propylene)-bis[N- methyl-2-hydroxyundecylamine] (12 ,R CH (CH R CH X (CH Z H) dihydrobromide (12.9 g., m.p. 176.0189.0C.).

EXAMPLE 48 Condensation of l'-undecene oxide and 1,4- butanediamine affords N,N'-( 1 ,4-butylene)-bis[2- hydroxyundecylamine] (I: R CH (CH R H, X (CH Z H).

EXAMPLE 49 Condensation of l-undecene oxide and 1,5-pentanediamine affords N,N-( l ,S-pentylene )-bis[ 2- hydroxyundecylamine] (I: R CH (CH R H, X -M5,

EXAMPLE 50 "Condensation of l-heptene oxide and 1,7-heptanediamine affords N,N-(1,7-heptylene)-bis[2- hydroxyheptylamine] (I: R CH ;(CH R. H, X 91, Z

EXAMPLE 51 In a manner similar to that of Example 1, condensation of l-heptene oxide (52 g.) and 1,8-octanediamine (32.8 g.) and two recrystallizations of the resulting product from methanol gave N,N"-( l ,8-octylene)- bis[Z-hydroxyheptylamine] (I: R CH (CH R H, X (CH Z H) (17.2 g., m.p. 128.0-132.8C.).

EXAMPLE 52 In a manner similar to that of Example 22, methylation of N,N-(l,8-octylene)-bis[2-hydr0xyheptylamine] (16.9 g.), treatment of the resulting product with hydrogen bromide and two recrystallizations of the resulting salt from isopropyl alcohol gave N,N-(l,8- octylene)-bis[N-methyl-2-hydroxyheptylamine] (l: R

. 12 CH (CH R CH X (CI-1 Z H) dihydrobromide (15.9 g., l77.0-l9 0.0C.).

EXAMPLE 5 3 EXAMPLE 55 Condensation of l-pentene oxide and 1,1 lundecanediamine affords N,N-( 1,1 1-undecy1ene)- bis[2-hydroxypentylamine] (I: R CH (CH R H, 2)11 Z EXAMPLE 56 Condensation of l-pentene oxide and 1,12-

dodecane'diamine affords N,N-( 1,1 2-dodecy1ene bis[2-hydroxypentylamine] (I: R CH3(CH2)2, R H, X=(CH2),2,Z=H.

EXAMPLE 57 Condensation of l-undecene oxide and l-methyl-'l',2- ethanediamine affords N,N'-(1,2-propylene)-bis[2- hydroxyundecylamine] (I: R CH (CH R H, X =-CH(CH )CH Z H). i i

.. EXAMPLE 58 Condensation of l-undecene oxide and 1 ,2-dimethyl- 1,2-ethanediamine affords N,N-(2,4-butylene)-bis['2- hydroxyundecylamine] (I: R CH3(CH2)Q, R H, X=

EXAMPLE s9 Condensation of I -pentene oxide and, 1,10-dimethyll',l0 -dedanediamine affords N,N '-(2,10-dodecylene)- bis'[ 2-hydroxypentylamine] (I: R CH ,(CH R H, X CH(CH )(CH CH(CH Z H).

' ExA PLEso Condensation of l-undecene oxide and 2'-methyl-l ,4- butanediamine affords N,N-(2-methyl-1,4-butylene)- bis[2-hydroxyundecylamine] (I: R CH (CH R H, X CH CH(CH -,)CH CH Z H).

' EXAMPLE 61 In a'manner similar to that of Example I, condensation of l-octene oxide (50 g.) ,and 1,4-cycl0hexylenebis(methylamine) (27.8 g.) and recrystallization of the resulting product from acetone gave N,N-(l,4- cyclohexylenebismethyl)-bis[2-hydroxyocty1amine] (I: R CH (CH R H, X

cu' cmcn cn cncu z. H), (12 g., m.p.-

EXAMPLE 6 2 In a manner similar to that of Example 1, condensation of l-decene oxide (two runs, 50 g. each) and 1,4- cyclohexylenebis(methylamine) (22.8 g. each run) and two recrystallizations of the products from acetone 13 gave N,N'-( 1,4-cyclohexylenebismethyl)-bis[2- hydroxydecylamine] (R CH (CH R H, X CH CH(CH CH CHCH Z H) (18.4 g., m.p. 92.0-98.8C.).

EXAMPLE 63 In a manner similar to that of Example I, condensation of l-decene oxide (96.6 g.) and cis-1,4-cyclohexylenebis(methylamine) (44.2 g.) and two recrystallizations of the resulting product from acetone gave N,N'- (cis-l ,4-cyclohexylenebismethyl)-bis[2-hydroxydecylamine] (l: R CH (CH R H, X cis- CH CH(CH CH CHCH Z H) (13.5 g., m.p. 72.6-77.4C.).

EXAMPLE 64 In a manner similar to that of Example 1, condensation of l-decene oxide (98.9 g.) and trans-1,4- cyclohexylenebis-(methylamine) (45.2 g.) and recrystallization of the resulting product from acetone gave N,N-(trans-1,4-cyclohexylenebismethyl)- bis[2hydroxydecylamine] (I: R CH (CH R H, X trans-CH CH(CH CH CHCH Z H) (23.3 g., m.p. 101.0-102.8C.).

EXAMPLE 65 In a manner similar to that of Example 22, methylation of N,N-(1,4-cyclohexylenebismethyl)-bis[2- hydroxydecylamine] and two recrystallizations of the resulting product from methanol gave N,N'-(l,4- cyclohexylenebismethyl)-bis[N-methyl-Z-hydroxydecylamine] (I: R CH (CH R H, X CH CH(CH CH,) CHCH Z H) (8.9 g., m.p. 6669C.).

EXAMPLE 66 In a manner similar to that of Example 1, condensation of l-dodecene oxide (50 g.) and 1,4-cyclohexylenebis(methylamine) (19.3 g.) and recrystallization of the resulting product from methanol gave N,N-(1,4- cyclohexylenebismethyl)-bis[2-hydroxydodecylamine] (I: R CH (CH R H, X

Z g., m.p. 93.096.0C.).

EXAMPLE 67 Condensation of l-decene oxide and cyclobutylidenebis(methylamine) affords N,N-(cyclobutylidenebismethyl)-bis [Z-hydroxydecylamine] (I: R CH (CH R H, X (CH CCH CH CH Z H). l l

EXAMPLE 68 Condensation of l-decene oxide and 1,2-cycloheptylenebis(methylamine) affords N,N-(l,2-cyclohep tylenebismethyl)-bis[2-hydroxydecylamine] (l: R CH (CH R H, x CH CH(CH ),,CHCH z H). l l

EXAMPLE 69 Condensation of l-decene oxide and l-(aminomethyl)-4-(2-aminoethyl)cyclohexane affords N,N'-[cyclohexylene-l -methyl-4-(2-ethyl )]-bis[2-hydroxydecylamine] (I: R CH (CH R H, X CH CH CH(CH CH CHCH Z H).

EXAMPLE 70 Condensation of l-decene oxide and l-(aminomethyl)-4 -(l-aminoethyl)cyclohexane affords N,N'-[cyclohexylenel -methyl-4-( l-ethyl ]-bis[2-hydroxydecylamine] (I: R CH (CH R H, X CH(CH )CH(CH CH CHCH Z H).

EXAMPLE 71 Condensation of l-decene oxide and l-(aminomethyl)-4-(4-aminobutyl)cyclohexane affords N,N-[cyclohexylene-l-methyl-4-(4-butyl)]-bis[2-hydroxbutenylene)diamine ydecylamine] (I: R CH (CH R H, X

EXAMPLE 72 Condensation of l-decene oxide and 1,4-phenylenebis-(methylamine) affords N,N-(1,4-phenylenebismethyl)-bis[2-hydroxydecylamine1 (I: R CH (CH R H, X 1,4-CH C H CH Z H).

EXAMPLE 73 Condensation of 1;decene oxide and trans-1,4-(2- affords N,N-[trans-1,4-(2- butenylene)]-bis-[2-hydroxydecylamine] (I: R CH (CH R H, X trans-CH CH==CHCH Z H).

EXAMPLE 74 Condensation of l-decene oxide and 1,4-(2- butynylene)-diamine affords N,N-[1,4- butynylene)]bis[2-hydroxydecylamine] (I: R

EXAMPLE 75 EXAMPLE 76 Condensation of N,N l ,4-cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] and o-tolyl isocyanate affords N,N-( 1 ,4-cyclohexylenebismethyl)- bis[N-methyl-2-hydroxydecylamine] bis(o-methylcarbanilate) (I: R CH (CH R CH X CH CH(CH CH CHCH Z CONHC H CH -o).

EXAMPLE 77 Condensation of N,N-(1,4-cyclohexylenebismethyl)-bis[N-methyI-2-hydroxydecylamine] and pbromophenyl isocyanate affords N,N'-(l,4-cyclohexylenebismethyl)-bis[N-methyl-Lhydroxydecylamine] bis(p-bromocarbanilate) (I: R CH (CH R CH;,, X CH CH(CH CH CHCH Z CONHC H Br-p).

EXAMPLE 78 Condensation of N,N'-(l,4-cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] and 4- chloro-o-tolyl isocyanate affords N,N'-(l,4-cycl0hexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] 15 bis(2-methyl-4-chlorocarbanilate) (I: R CH (CI-I CH X CH CH(CH CH CHCI-I Z CONHC H CH -2-Cl-4).

EXAMPLE 79 Condensation of N,N-(1,4-cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] and 5- chloro-2,4-dimethoxyphenyl isocyanate affords N,N (l,4-cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] bis(5-chloro-2,4-dimethoxycarbanilate) I: R CI-I;,(CI-I R CH X CH Cl-I(Cl-I CH CI-ICI-l Z CONHC I-I (OCII 2,4-Cl-5).

EXAMPLE 80 Condensation of N,N'-(1,4-cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] and m-(trifluoromethyl)-phenyl isocyanate affords N,N'-(l,4- cyclohexylenebismethyl)-bis-[N-methyI-Z-hydroxydecylamine] bis[m-(trifluoromethyl)-carbanilate] (I: R CH (CH R CH X CH CH(CI-I CI-I Cl-ICI-I Z CONHC H CF -m).

EXAMPLE 81 Condensation of N,N'-(1,4-cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] and pacetamidophenyl isocyanate affords N,N'-(l,4- cyclohexylenebismethyl)-bis[N-methyl-Z-hydroxydecylamine] bis(p-acetamidocarbanilate) (I: R CH (CH R CH X CH CI-I(CI-I CI-I Cl-ICH Z CONHC I-I -NI-ICOCH -p).

EXAMPLE 82 Condensation of N,N'-(1,4-cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] and mnitrophenyl isocyanate affords N,N-( l ,4-cyclohexylenebismethyl)-bis[N-rnethyl-2-hydroxydecylamine] bis(m-nitrocarbanilate) (I: R CI-I;,(CH R CH X CH CH(CH CH CHCH Z CONHC H NO m).

EXAMPLE 83 Condensation of N,N-(1,4-cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] and p-(methylsulfonyl)phenyl isocyanate affords N,N'-(l,4- cyclohexylenebismethyl)-bis[N-methyl-2-hydroxydecylamine] bis[p-(methylsulfonyl)carbanilate] (I: R

CH CH(CI-I CI-I CHCI-I Z p)- Examples 84-90 are N,N-dioxides of the formula HO R I? ('i)ll R(LHCH -fi-XHCH CHR (Formula IV).

EXAMPLE 84 Hydrogen peroxide (30%, I64 ml.) was added dropwise with stirring to a solution of N,N-(l,6-hexylene)- bis[N-methyl-2-hydroxyundecylamine] (51.6 g.) in alcohol (200 ml.). The temperature was maintained at about 25C. with cooling during the addition. The solution was allowed to stand overnight at room temperature. A small amount of palladium-on-carbon was added and the mixture was allowed to stand overnight Table III Bacteriostatic Bactericidal Microorganism concentration concentration (iv-pm (P-P-m.)

Staphylococcus aureus I0 25 Eberthella typhi l00 Clostridium welchii I0 10 Pseudomonas aeruginosa 100 100 EXAMPLE In a manner similar to that of Example 84, oxidation of N,N l ,6-hexylene)-bis[N-methyl-Z-hydroxyheptylamine] (20.2 g.) and two recrystallizations of the resulting product from acetone gave N,N-(l,6-hexylene )-bis[N-methyl-2-hydroxyheptylamine] N,N dioxide (IV: R CH (CI-I R' CH X (CI-I (6.0 g., m.p. l48.0) C.).

EXAMPLE 86 In a manner similar to that of Example 84, oxidation of N,N'-( 1 ,6-hexylene)-bis[N-methyl-2-hydroxyoctylamine] (30.3 g.) and recrystallizationof the resulting product from acetonitrile gave N,N'-( l ,6-hexylene)- bis[N-methyl-2-hydroxyoctylamine] N,N-dioxide (IV: R CH (CI-I R CH x cup (26.1 g., m.p. l43.8l45.5C.).

EXAMPLE 87 In a manner similar to that of Example 84, oxidation of N,N l ,6-hexylene )-bis[N-methyl-2-hydroxynonylamine] and recrystallization of the resulting product from acetonitrile gave N,N-( l ,6-hexylene)- bis[N-methyl-2-hydroxynonylamine] N,N-dioxide (IV: R CH (CI-I R CH,,, X (CI-I9 (19.3 g., m.p. 155.0l57.6C.).

EXAMPLE 88 In a manner similar to that of Example 84, oxidation of N,N'-( l ,6-hexylene )-bis[N-methyl-2-hydroxydecylamine] (31.7 g.) and two recrystallizations of the resulting product from acetone-methanol gave N,N- l ,6-hexylene )-bis[N-methyl-2-hydroxydecylamine] N,N-dioxide (IV: R CH (CI-I R CH X (CH (4.0 g., m.p. l620.0166.0C.).

EXAMPLE 89 In a manner similar to that of Example 84, oxidation of N,N'-( l ,6-hexylene )-bis[N-methyl-2-hydroxydodecylamine] (40 g.) and two recrystallizations of the resulting product from acetone-methanol gave N,N'-( l ,6-hexylene )-bis[N-methyl-2-hydroxydodecylamine] N,N'-dioxide (IV: R CH (CH R CH X (CH (l0.4 g., m.p. l63.6l66.0C.).

EXAMPLE 90 In a manner similar to that of Example 84, oxidation of N,N'-(1,6-hexylene)-bis[N-methyl-2-hydroxytetradecylamine] (28.2 g.) and two recrystallizations of the resulting product from acetone-methanol gave N,N-(1,6'hexylene)-bis[N-methyl-Z-hydroxytetradecylamine] N,N-dioxide (IV: R CH (CHhd 2) R CH,,, X (CH (8.8 g., m.p. 150.0l55.0C.).

Examples 91-98 are N,N-diammonium quaternary salts of the formula A mixture of N,N-(1,6hexylene)-bis[N-methyl-2- hydroxyundecylamine] (10 g.), methyl chloride (34 g.) and acetonitrile ml.) was heated in a bomb (6065C., 4 hr.). The resulting product (3.6 g.) was recrystallized from acetonitrile affording N,N-(1,6- hexylene)-bis[N,N-dimethyl-Z-hydroxyundecylammonium]dichloride (V: R CH (CH R R" CH X cup Y CI 7.0 g., m.p. 171.0l74.8C.).

Table IV shows the results of the antibacterial testing in vitro of N,N-(l,6-hexylene)-bis[N,N-dimethyl-2- hydroxyundecylammonium ldichloride.

Table IV Bacteriostatic Bactericidal Mwroorgamsm concentration concentration (p.p.m.) (p.p.m.)

Staphylococcus aureus 2.5 2.5 Eberthella cali 50 50 Pxeudomonas aeruginosa 50 100 Proteus vulgaris 100 EXAMPLE 92 in a manner similar to that of Example 91, quaternerization of N,N-( l ,6-hexylene)-bis[N-methyl-2-hydroxydecylamine] (two runs, 10 g. each) with methyl chloride ml. one run, 28 g. other run) and recrystallization of the combined products from acetonitrile gave N,N'-( l ,6-hexylene)bis[N,N-dimethyl-Z-hydroxydecylammonium]dichloride (V: R CH (CH R R" CH X (CH Y Cl) (18.7 g., m.p. l7l.O-l74.0C.).

EXAMPLE 93 Ouaternerization of N,N'-(1,6-hexylene)-bis[N- methyl-Z-hydroxydecylamine] with methyl iodide affords N,N-( l,6-hexylene)-bis[N,N-dimethyl-Z- hydroxydecylammonium]diiodide (V: R CH ',(CH R R" CH X 011 Y =1 EXAMPLE 94 Quaternerization of N,N-(l,6-hexylene)-bis[N- EXAMPLE 95 Quaternerization of N,N 1,6-hexylene )-bis[N- methyl-N-propyl-2-hydroxydecylamine] with propyl bromide affords N,N'-(1,6-hexylene)-bis[N-methyl-N- propyl-2-hydroxydecylammonium] dibromide (V: R 3( 2)7, 3 3( 2)2 X 2)s, Y Br).

EXAMPLE 96 Quaternerization of N,N-(1,6-hexylene)-bis[N- methyl-2-hydr0xydecylamine] with isobutyl iodide affords N,N-(1,6-hexylene)-bis{N-isobutyl-N-methyl-2- hydroxydecylammonium] diiodide (V: R =CH;,(CH R CH R (CH CHCH X (CH Y =1).

EXAMPLE 97 In a manner similar to that of Example 91, quaternerization of N,N'-(1,6-hexylene)-bis[N-methyl-2-hydroxydodecylamine] (10 g.) with methyl chloride (34 g.) and recrystallization of the resulting product from acetonitrile gave N,N-(l,6-hexylene)-bis[N,N-dimethyl- 2-hydroxydodecylammonium]dichloride (V: R

methyl-2-hydroxydecylamine] with ethyl p-toluenesul- I fonate affords N,N-(1,6-hexylene)-bis[N-ethyl-N- methyl-2-hydroxydecylammonium] bis(p-toluenesulfonate) (V: R CH (CH R CH R CH CH X fis Y s s i a'Pl g., m.p. l76.6-l80.0C.).

EXAMPLE 98 A mixture of N,N-(l,6-hexylene)-bis[N-methyl-2- hydroxyheptylamine] (5g.), benzyl bromide (4.7 g.) and hexane (60 ml.) was heated under reflux (for 5 hr. Acetonitrile (20 ml.) was added and refluxing was continued (for 5 hr.). The solvents were stripped and the residue was recrystallized from ethylene dichloride, affording N,N-( l ,6-hexylene)-bis[N-benzyl-N-methyl- Z-hydroxyheptyl-ammonium]dibromide (V: R CH (CH R CH R C H CH X (CH Y Br) (3.5 g., m.p. l27.0-129.0C.)

We claim: 1. N,N-( l ,6-hexylene)-bis[2-hydroxyundecylamine1diglycolate.

2. N,N-( l ,6-hexylene )-bis[N-methyl-Z-hydroxyundecylamine] dihydrobromide.

3. N,N-(1,6-hexylene)-bis[N-methyl-2-hydroxyheptylamine] dihydrobromide.

4. N,N'-( l,6-hexylene)-bis[N-methyl-Z-hydroxyoctylamine] dihydrobromide.

5. N,N'-(1,6-hexylene)-bis[N-methyl-2-hydroxynonylamine] dihydrobromide.

6. N ,N-( 1 ,6-hexylene)-bis[N-methyl-2-hydroxydecylamine] dihydrobromide.

7. N ,N'-( 1 ,6-hexylene)-bis[N-methyl-2-hydroxydodecylamine] dihydrobromide.

8. N,N'-ethylenebis[N-methyl-Z-hydroxydecylamine] dihydrobromide.

9. N,N-ethylenebis[N-methyl-2-hydroxyundecylamine] dihydrobromide.

10. N,N'-ethylenebis[N-methyl-2-hydroxydodecylamine] dihydrobromide.

11. N ,N'-(1,3-propylene)-bis[N-methyl-2-hydroxynonylamine] dihydrobromide.

12. N ,N-( 1 ,3-propylene)-bis[N-methyl-2-hydroxydecylamine] dihydrobromide.

13. N ,N-( l,S-propylene)-bis[N-methyl-Z-hydroxyundecylamine] dihydrobromide.

14. N,N'-(1,8octylene)-bis[N-methyl-2-hydroxyheptylamine] dihydrobromide. 

1. N,N''-(1,6-HEXYLENE)-BIS-(2-HYDROXYUNDECYLAMINE)DIGLYCOLATE.
 2. N,N''-(1,6-HEXYLENE)-BIS(N-METHYL-2-HYDROXYUNDECYLAMINE) DIHYDROBROMINE.
 3. N,N''-(1,6-hexylene)-bis(N-methyl-2-hydroxyheptylamine) dihydrobromide.
 4. N,N''-(1,6-hexylene)-bis(N-methyl-2-hydroxyoctylamine) dihydrobromide.
 5. N,N''-(1,6-hexylene)-bis(N-methyl-2-hydroxynonylamine) dihydrobromide.
 6. N,N''-(1,6-hexylene)-bis(N-methyl-2-hydroxydecylamine) dihydrobromide.
 7. N,N''-(1,6-hexylene)-bis(N-methyl-2-hydroxydodecylamine) dihydrobromide.
 8. N,N''-ethylenebis(N-methyl-2-hydroxydecylamine) dihydrobromide.
 9. N,N''-ethylenebis(N-methyl-2-hydroxyundecylamine) dihydrobromide.
 10. N,N''-ethylenebis(N-methyl-2-hydroxydodecylamine) dihydrobromide.
 11. N,N''-(1,3-propylene)-bis(N-methyl-2-hydroxynonylamine) dihydrobromide.
 12. N,N''-(1,3-propylene)-bis(N-methyl-2-hydroxydecylamine) dihydrobromide.
 13. N,N''-(1,3-propylene)-bis(N-methyl-2-hydroxyundecylamine) dihydrobromide.
 14. N,N''-(1,8-octylene)-bis(N-methyl-2-hydroxyheptylamine) dihydrobromide. 